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I'm Canadian and my 90-day Schengen stay ends on June 11th. However my flight to Sofia, Bulgaria, is in the morning of June 12th.

So I figured in order to not break the 90-day rule, I will simply arrive at the airport and pass the security check before midnight. I figure this should make me comply 100%.

However I am wondering if my passport will even get stamped in Spain. Or will I only get an entry stamp from Bulgaria on the 12th? Thus making it look like I overstayed by one day.

It really wasn't possible for me to fly to Sofia on the 11th or else I would have done that.

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    You will get a Schengen exit stamp as you leave Spain. Unless your flight to Bulgaria is very early in the morning (say, 0200 or earlier), I don't think you can count on being allowed to pass border control in time. – Andrew Lazarus May 30 '18 at 16:26
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    @DavidRicherby getting an exit stamp usually qualifies as leaving a country. – alamar May 30 '18 at 16:30
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    Passing the security checkpoint is completely irrelevant for this case. OP will have to pass exit immigration control on the 11th, although the flight is on the 12th. If that will be possible will depend on which airport you are flying from and perhaps which airline you are using. Not all airports are open at night and will allow this and on some low-traffic airports, immigration checkpoints are only open only in immediate connection with departure or arrival of non-schengen flights. – Tor-Einar Jarnbjo May 30 '18 at 18:55
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    @DavidRicherby the Schengen system currently works purely on the passport stamp dates as specified in Article 8 of the Schengen Borders Code. Obviously you're right about legal presence, but as a matter of practical implementation, nobody seems to be making that case. – phoog May 30 '18 at 20:48
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    verperknight: you can solve your problem by leaving the Schengen area for at least one full calendar day between now and June 11th, if your budget and calendar allow. I believe you could use Gibraltar or Andorra for this; Morocco and the UK or Ireland would certainly work but require more time and money. You have to stay outside Schengen for two consecutive midnights, so, for example, if you leave the Schengen area on June 2nd, you must return on or after the 4th. This means that the 3rd is no longer counted towards your 90-day limit. – phoog May 30 '18 at 20:57
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This is dependent on the airport, and you're not guaranteed to get a stamp at all. It would be a very good idea to find some other way of avoiding the 90 day limit.

Please note that being past the security checkpoint is not the same as being past immigration control. Smaller airports that have domestic/intra-Schengen flights and international ones flying out of the same terminal are more likely to be doing immigration control at the gate, in which case you will very likely be unable to get an exit stamp until the gate is open for boarding for your flight.

Anecdotally, I flew VLC-LGW recently, where the immigration control was at the gate but not manned, so nobody on that flight received an exit stamp at all. It's also not the first exit stamp I've missed, so I wouldn't make any plans dependent on having that stamp.

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    (+1) Excellent point about checks at the gate, that's a factor to keep in mind! To clarify what you wrote about exit stamps, it's important to note that what happened to you in Valencia is a blatant disregard for the rules (even if it appears to be quite common). The Schengen Borders code is crystal clear, if you need stamps at all, you have to get one when exiting the Schengen area. It's not as critical when you are not skirting the 90-day limit but it is in theory what Schengen border guards should use to enforce duration of stay limits. – Relaxed May 31 '18 at 9:22

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